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H sp sp 1 sigma-binding dannet ved sp-sp-overlapping.

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`‰| ˆ

E+R 7

fd¹

E+R 7 c

€

–‹R

( hh j

E+R 7

E+R

7

ˆ^|

c0}~

J

~€C~

(6)

Løsning oppgave 3.

a)

b)

C C H

H sp sp 1 sigma-binding dannet ved sp-sp-overlapping.

2 pi-bindinger hver dannet ved p-p-overlapping.

Trippelbinding:

2pz 2pz 2py 2py

sp sp

sp2-hybridisert C, N og O.

O

H

C N

Resonansbidragene:

O

H C N O

H

C N

(7)

c)

d) i)

ii)

Ett av de to produktene eller begge godtas som svar.

H C CH

O

CH C O

O CH 2 CH 2 CH 3

1 2 3 4

Propyl 4-oxo-but-2-enoat (propyl 4-oxo-2-butenoat)

3.

2.

1.

COOH OH H

H HO

COOH COOH H HO

OH H

COOH COOH

OH H

OH H

COOH

COOH OH H

OH H

COOH 1.

Motsatt konfigurasjon ved ett av to kirale C-atomer.

Motsatt konfigurasjon ved ett av to kirale C-atomer.

1. og 2. er diastereomere:

1. og 3. er diastereomere:

COOH H HO

OH H

COOH

COOH OH H

H HO

COOH

2. 3.

2. og 3. er enantiomere:

Motsatt konfigurasjon ved alle kirale C-atomer.

COOH O

COOH OH oxidasjon

COOH O O COOH 1.

COOH OH H

OH H

COOH

+

(8)

iii)

B A

B A

S

4 3 2

1

OH R'' H R''

OH H

COOH

R

3

4 2 1

R' OH

COOH H

COOH OH H

R'

B A

COOH OH H

OH H

COOH

HOOC

COOH OH H

OH H

COOH

A B

R

S

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